Desc: Erotica Sex Story: Chapter 1: Foundations - Jake, a 17-year old highschooler, has a simple little contest with his two best friends Dylan and Robby that he's been playing since freshman year: who can pop the most teenage cherries by the time they graduate? To spice things up a bit, they added a few interesting rules that let them score bonus points. And of course, you can hardly call it a contest without some sort of prize. Luckily, by the time they graduate, all three boys will have little sisters starting their freshman year...

With a final grunt of effort, Jake buried the last inch of his cock into the clenching asshole of the whimpering girl beneath him. It had taken the better part of an hour to work his way into her anal cavity, despite a generous amount of Astroglide easing the way, as every inch he had had to pause to allow Lisha’s body to adjust. Literally every inch; it took a full seven pauses before he was finally embeded. Relieved that he could finally get started- motionless sex wasn’t very stimulating, no matter how tight the hole was- Jake adjusted his knees and began to pull his hips backwards.

“Oh, oh, hold on, stop...” Lisha gasped out, taking her mouth off the pillow she had been biting.

Suppressing a sigh, Jake dutifully paused his retreat. He had barely pulled out half an inch before she stopped him and as pleasant as her insides felt wrapped around his shaft, he was becoming increasingly impatient to get to the good part.

Granted, the entire situation was partially his fault. He had smooth-talked his way into Lisha’s ass without setting up any prepwork; no thumbs slyly popped in during sex, no buttplug training to subty stretch and train her anus to accept his seven inch cock, just a few whispered platitudes and a large dollop of the Astroglide he kept at the bottom of his backpack.

It’s not as if he had expected the going to be easy, of course. In fact, he hadn’t actually expected Lisha to even seriously consider the idea. After all, the small red stain on her cotton-white sheets (tossed onto the floor after the act) from just a few hours ago were a color-coded marker of her sexual inexperience, but in all honesty Jake had grown somewhat tired of Lisha. So he’d decided he may as well go for broke.

Jake had been casually working on Lisha for a few weeks before he finally got to pop her. She was cute enough, but nothing special. A 15-year old Sophomore from the same highschool, Westwood High, she was about as generically attractive as a teenager could be: white, midwestern skin tone, straight brown hair worn down to her shoulders, nice B-sized tits with normal, pink nipples and, somewhat unfortunately, a flat white girl ass. She was also supremely uninteresting. The entirety of Jake’s seduction had been based on his seniority and good lucks, relying on mysterious, silent smiles in her direction and banal conversations in the school hallways, conversations about nothing at all since as far as Jake could tell, Lisha had absolutely no hobbies. No particular likes or dislikes. So average and boring that Jake normally wouldn’t have bothered.

But still. She’d been a virgin. A point was a point. If he managed to somehow smuggle the blood-stained sheets out of the house, he’d get an extra point, since actual bleeders were pretty rare, most girls busting their cherries from gymnastics or biking or a little too much enthusiasm with certain vegetables. And he was, after all, seven- or rather, six and a half- inches into her rectum, so maybe she wasn’t quite as boring as he’d thought. Maybe.

Bringing himself back to the present, he considered the situation with an expereinced eye. Lisha clearly wasn’t going to adjust to his girth in any reasonable amount of time, so he decided to simply take matters into his own hands.

Firmly taking an asscheek in each hand, Jake first thurst forward slightly, embedding the half-inch of dick he’d extracted back inside, earning a distinctly unladylike grunt from Lisha, muffled once again since her face was shoved into her pillow. Then, ignoring Lisha’s mumbled protests, he slowly but steadily pulled out until only the head of his cock remained inside its’ sheath. Lisha let out a heavy groan, picking her head up and starting to turn her face back towards him. It seemed she thought he was just going to give up and pull out.

Silly girl. She’d learn.

Shifting his hips a bit so he could angle straight downwards, Jake thurst the entirety of the dick up the poor teen’s asshole before she could register what was happening. With a squawk Lisha attempted to pull forward and away, but Jake lifted his left hand off her flat ass and onto the back of her head, gently but firmly grasping a fistful of hair.

Then, leaning his body over her back, he forcefully shoved her face into the pillow while he took his pleasure.

It wasn’t the easiest way, obviously. At first Lisha squirmed wildly, trying to lift her head or else at least knock him off his stride. But Jake was not only much larger and stronger than the poor girl, he also had leverage on his side. Keeping her pinned down while he sawed his cock in and out of her ass was a bit troublesome, but it was better than taking all day to get his rocks off.

Finally, after about five minutes of solidly pounding her teenage asshole, Jake thurst forward a final time, letting his grip on Lisha’s head relax as he spewed a load inside of her. Not that there was all that much left to give; he’d already cum three times today, twice in Lisha’s formerly virgin pussy and once earlier in the day, at lunchtime, down the throat of a cheerleader named Amber.

Not that Lisha knew that, of course.

So his fourth load of the day wouldn’t exactly be breaking any record books, but it was enough that when he pulled his softening dick from her lewdly stretched anus a small trickle of white flowed out of her ass and down to her pussy, joining the (much diminished after a hard anal fucking) trickle leaking from her cunt.

Even without his hand keeping her there, Lisha remained facedown on her bed as Jake got up and started getting dressed. He could see the rise and fall of her breathing, so he wasn’t overly concerned. She even made a pretty picture, face down and ass up. In fact, since she seemed so out of it, Jake pulled his phone out of his jeans’ pocket and snapped a few photos. Just for posterity, of course.

Now fully dressed, he gave a gentle sideways push on Lisha’s butt, rolling her to her side so he could see her face. Bending down, he gave her a quick peck on the cheek.

“That was great, baby,” Jake whispered. “Really great. I’ll see you at school tomorrow, ok?”

At first, Lisha made no response. Then, slowly, she managed a small, trembling smile and a nod. Taking that as affirmation that all was well, he gave her another kiss on the cheek and then, at the last moment remembering to stuff the stained sheets into his backpack, he strode out her bedroom door and on his way. Or at least, that was his intention.

As he left Lisha’s bedroom, he nearly collided with the short figure that had apparently been crouching and listening at the door. Caught like a deer in headlights, the peeping (eavesdropping?) Tom- or in this case peeping Tess, since the culprit was none other than Lisha’s tomboy little sister Tessa- said nothing, didn’t even make an excuse as Jake shut the door behind him.

Jake took a moment to observe the little pervert. He knew Lisha had a sister, of course, since it was one of the few topics they could even pretend to carry a conversation about, but he’d never met her since she was still in middle school. Eight grade, if he remembered right.

Tessa seemed to be just as Lisha had described her; a gangly thirteen year old, all elbows and knees with short hair and grass burns on her arms. Even so, she was still very evidently a girl ... and a point was a point, after all...

But not today. Firstly, his balls were drained dry. Secondly, she was a bit young even for him. Not that she’d be the first middle schooler he popped since the start of the contest (hell, not even the youngest, though he wasn’t proud of that), but he preffered his partners to be firmly on the path through puberty, not right at the starting gate. Still, a little groundwork didn’t cost anything, and could pay off sometime down the road.

He crouched down on his heels to bring him eye level with the barely-past-preteen.

At first it seemed like Tessa would deny it, but he held her gazy until she silently nodded yes.

“Did you just listen? Or did you steal a peek while we were busy?” he asked even more softly, subtling closing the distance between their faces.

She looked down and away guiltily, until he gently cupped her chin and brought her eyes back to his, her irises starting to widen.

“Did you like what you saw?”

Her blush answered for her.

“Would you like to ... give it a try?” Jake’s lips were mere inches from Tessa’s and she seemed unable to break from his gaze, a mouse hypnotized by a python.

For a full minute, she did nothing, said nothing. Then slowly, shakily, she nodded.

Jake leaned forward until there was barely half a inch seperating their lips. He could smell her breath, sweet from some flavored candy as she breathed harder and faster under his gaze.

“In that case...” he murmered, tilting his head ever so lightly to the right. Tessa did the same, closing her eyes and trembling slightly.

“Come find me when you get to highscool,” Jake said, suddenly no longer speaking softly. Abruptly, he stood up, patted her on the head, and clambered down the hallway, down the stairs and out Lisha’s front door without so much as a backwards glance.

Stepping outside into the fading sunlight, Jake stretched luxuriously and headed towards his car, a well-worn but still very cool black Jeep Wrangler. Hopping into the front seat, he felt something poking uncomfortably in his back pocket. Lifting himself off the seat for a moment, he reached back and withdrew a foil-wrapped condom, tossing it into his glove compartment. He’d been prepared, naturally but Lisha’d never mentioned it so he felt no need to bring it up.

He wasn’t actually sure if Lisha was on the pill or not- it’d never come up- so he didn’t know if the two loads he’d left in her cunt was a risk or not. Not that he particularly cared either way.